US3356710A - Ethyl nu-benzoyl nu (2-chloroethyl) carbamate and process of preparation - Google Patents
Ethyl nu-benzoyl nu (2-chloroethyl) carbamate and process of preparation Download PDFInfo
- Publication number
- US3356710A US3356710A US346093A US34609364A US3356710A US 3356710 A US3356710 A US 3356710A US 346093 A US346093 A US 346093A US 34609364 A US34609364 A US 34609364A US 3356710 A US3356710 A US 3356710A
- Authority
- US
- United States
- Prior art keywords
- ethyl
- benzoyl
- chloroethyl
- carbamate
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 title claims description 14
- 238000000034 method Methods 0.000 title description 9
- 238000002360 preparation method Methods 0.000 title description 4
- LIJLYNWYKULUHA-UHFFFAOYSA-N 2-chloroethyl carbamate Chemical compound NC(=O)OCCCl LIJLYNWYKULUHA-UHFFFAOYSA-N 0.000 title 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 7
- -1 2-CHLOROETHYL Chemical class 0.000 claims description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YDPPPCVREIZVSA-UHFFFAOYSA-N (2-ethylaziridin-1-yl) formate Chemical compound C(=O)ON1C(C1)CC YDPPPCVREIZVSA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 241000238682 Amblyomma americanum Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Definitions
- the present invention is directed to ethyl N-benzoyl N(2-chloroethyl)carbamate having the formula o ornorn-o-ii-rg-c-Q ClCHzCI-In H CHaCHr-O-C-N
- the amounts of the reagent to be employed are not critical, some of the desired product being obtained when employing the reagents in any proportions. In a preferred method of operation, good results are obtained when employing substantially equimolecular proportions of the ethyl l-aziridinyl formate and the acid chloride.
- the reaction takes place smoothly between the temperatures of 25 and 150 C. with the production of the desired product.
- the preferred temperature range is between the temperatures of and 120 C.
- the reaction conveniently can be carried out in an inert solvent such as benzene, tollluene, dioxane and aliphatic ethers such as diethyl et er.
- the ethyl l-aziridinyl formate and benzoyl chloride can be combined in any convenient fashion.
- the benzoyl chloride is maintained with stirring at a temperature in the reaction temperature range while the ethyl l-aziridinyl formate is added slowly portionwise over a short period of time.
- the reaction mixture is processed by conventional procedures to obtain the desired product.
- the low boiling constituents are removed by distillation at reduced pressure, leaving the ethyl N-benzoyl N-(Z-chloroethyl ⁇ carbamate product as a residue. This residue may be employed in pesticidal compositions or further purified by vacuum distillation.
- Ethyl l-aziridinyl formate (41 grams; 0.36 mole) was added dropwise to benzoyl chloride (120 grams; 0.86 mole) at to C. over a period of one and onehalf hours. During the addition, the reaction mixture was stirred continuously and maintained at a temperature of 100 to 115 C. Following the reaction period, the excess benzoyl chloride was removed by distillation at reduced pressures. The liquid residue remaining after the distillation was fractionally distilled under vacuum and the ethyl N- benzoyl N(2-chloroethyl)carbamate product collected at between 107 and 109 C. under 0.4 millimeter of pressure.
- the compound of the present invention is useful as an insect repellent and a pesticide for the control of various plant and animal pests.
- the unmodified compound can be employed.
- the compound can be dispersed on an inert finely divided solid and the resulting preparation employed as a dust.
- such preparation can be dispersed in water with or without the aid of a wetting agent and the resulting aqueous dispersions employed as sprays.
- the compound can be employed in oil or other solvent, or as a constituent of a solvent in water or water in solvent emulsion, or an aqueous dispersion thereof which can be applied as a spray, drench, or wash.
- liquid compositions of ethyl N-benzoyl N(2 chloroethyl) carbamate at concentrations of 1 gram per 100 milliliters of ultimate mixture gave 100 percent kills of lone star tick.
- a method comprising reacting together benzoyl chloride and ethyl-l-aziridinyl formate in the presence of an inert organic solvent as a reaction medium and at a temperature of from 25--150 C.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
3,356,710 Patented Dec. 5, 1967 ICC ETHYL N-BENZOYL N(2-CHLOROETHYL)CAR- BAMATE AND PROCESS OF PREPARATION Leonard Levine, Lake Jackson, Tex., assignor to The Dow Chemical Company, Midland, Micln, a corporation of Delaware No Drawing. Filed Feb. 20, 1964, Ser. No. 346,093
2 Claims. (Cl. 260-471) ABSTRACT OF THE DISCLOSURE Ethyl N-benzoyl N(2-chloroethyl)carbamide useful as a pesticide and a method which comprises reacting together benzoyl chloride and ethyl-l-aziridinyl formate in the presence of an inert organic solvent and at a temperature of from 20-150" C.
The present invention is directed to ethyl N-benzoyl N(2-chloroethyl)carbamate having the formula o ornorn-o-ii-rg-c-Q ClCHzCI-In H CHaCHr-O-C-N The amounts of the reagent to be employed are not critical, some of the desired product being obtained when employing the reagents in any proportions. In a preferred method of operation, good results are obtained when employing substantially equimolecular proportions of the ethyl l-aziridinyl formate and the acid chloride. The reaction takes place smoothly between the temperatures of 25 and 150 C. with the production of the desired product.
However, the preferred temperature range is between the temperatures of and 120 C. The reaction conveniently can be carried out in an inert solvent such as benzene, tollluene, dioxane and aliphatic ethers such as diethyl et er.
In carrying out the reaction the ethyl l-aziridinyl formate and benzoyl chloride, can be combined in any convenient fashion. However, in a preferred procedure the benzoyl chloride is maintained with stirring at a temperature in the reaction temperature range while the ethyl l-aziridinyl formate is added slowly portionwise over a short period of time. Following the reaction, the reaction mixture is processed by conventional procedures to obtain the desired product. In a convenient procedure, the low boiling constituents are removed by distillation at reduced pressure, leaving the ethyl N-benzoyl N-(Z-chloroethyl} carbamate product as a residue. This residue may be employed in pesticidal compositions or further purified by vacuum distillation.
Ethyl l-aziridinyl formate (41 grams; 0.36 mole) was added dropwise to benzoyl chloride (120 grams; 0.86 mole) at to C. over a period of one and onehalf hours. During the addition, the reaction mixture was stirred continuously and maintained at a temperature of 100 to 115 C. Following the reaction period, the excess benzoyl chloride was removed by distillation at reduced pressures. The liquid residue remaining after the distillation was fractionally distilled under vacuum and the ethyl N- benzoyl N(2-chloroethyl)carbamate product collected at between 107 and 109 C. under 0.4 millimeter of pressure. Infrared analysis confirmed the identity of the product as ethyl N-benzoyl N(2-chloroethyl)carbamate having a refractive index n/D of 1.5240 at 25 C. The product was found to have chlorine and nitrogen contents of 13.88 percent and 5.48 percent, respectively, as compared with the theoretical contents of 13.82 percent and 5.62 percent, respectively.
The compound of the present invention is useful as an insect repellent and a pesticide for the control of various plant and animal pests. For such uses, the unmodified compound can be employed. Alternatively, the compound can be dispersed on an inert finely divided solid and the resulting preparation employed as a dust. Also, such preparation can be dispersed in water with or without the aid of a wetting agent and the resulting aqueous dispersions employed as sprays. In other procedures, the compound can be employed in oil or other solvent, or as a constituent of a solvent in water or water in solvent emulsion, or an aqueous dispersion thereof which can be applied as a spray, drench, or wash. In representative operations, liquid compositions of ethyl N-benzoyl N(2 chloroethyl) carbamate at concentrations of 1 gram per 100 milliliters of ultimate mixture gave 100 percent kills of lone star tick.
I claim:
1. Ethyl N-benzoyl N(2-chloroethyl)carbamate.
2. A method comprising reacting together benzoyl chloride and ethyl-l-aziridinyl formate in the presence of an inert organic solvent as a reaction medium and at a temperature of from 25--150 C.
References Cited UNITED STATES PATENTS 3,260,590 7/1966 Fischer 260-471 LORRAINE A. WEINBERGER, Primary Examiner. L. THAXT N, As i tant Examiner.
Claims (1)
1. ETHYL N-BENZOYL N(2-CHLOROETHYL)CARBAMATE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US346093A US3356710A (en) | 1964-02-20 | 1964-02-20 | Ethyl nu-benzoyl nu (2-chloroethyl) carbamate and process of preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US346093A US3356710A (en) | 1964-02-20 | 1964-02-20 | Ethyl nu-benzoyl nu (2-chloroethyl) carbamate and process of preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3356710A true US3356710A (en) | 1967-12-05 |
Family
ID=23357912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US346093A Expired - Lifetime US3356710A (en) | 1964-02-20 | 1964-02-20 | Ethyl nu-benzoyl nu (2-chloroethyl) carbamate and process of preparation |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3356710A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3260590A (en) * | 1962-12-21 | 1966-07-12 | Fmc Corp | Herbicidal method |
-
1964
- 1964-02-20 US US346093A patent/US3356710A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3260590A (en) * | 1962-12-21 | 1966-07-12 | Fmc Corp | Herbicidal method |
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